Acetoacetic Acid → 10-(Cholest-5-en-3beta-oxy)decanal

HRID 1471359Notes

Reaction equation

HRID 1471359 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16]([CH2:17][C@@H:18]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][OH:39])[CH2:19][CH2:20]2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].CC(CC(O)=O)=O>ClCCl>[CH3:3][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16]([CH2:17][C@@H:18]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH:38]=[O:39])[CH2:19][CH2:20]2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:1]

Participants

4

Reactant 2

HCID 96Acetoacetic AcidHCID 86665351HCID 86665351, compound

Product 1

HCID 8666535010-(Cholest-5-en-3beta-oxy)decanal

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 100 mL round-bottomed flask was solid supported 2,2,6,6-Tetramethyl Piperidinyloxy, Free Radical (0.5 g, 1.1 mmol/g, 0.553 mmol) and 10-(Cholest-5-en-3β-oxy)decan-1-ol (3.00 g, 5.53 mmol) suspended in dichloromethane (20 ml) to give a colorless suspension. lodobenzene diacetate (1.958 g, 6.08 mmol) was added to the mixture, which was allowed to stir overnight at room temperature. The reaction mixture was filtered and the solid support washed with DCM. The combined filtrate was washed with saturated sodium thiosulfate (2×20 mL) and brine (1×20 mL). The organic phase was dried over Na2SO4, filtered and concentrated. The resultant oil was purified via column chromatography with 100% DCM as mobile phase to give 2.70 g (90%) of a colorless wax. 1H NMR (300 MHz, CDCl3) δ0.69 (3H, s); 0.84-1.74 (47H, m); 1.76-2.09 (5H, m); 2.12-2.26 (1H, m); 2.32-2.40 (1H, m); 2.44 (2H, dt, J=7.4, 1.9 Hz); 3.14 (1H, tt, J=11.2, 4.4 Hz); 3.46 (2H, t, J=6.9 Hz); 5.35 (1H, d, J=5.3 Hz); 9.78 (1H, t, J=1.9 Hz).

Workup

  1. customIn a 100 mL round-bottomed flask was
  2. customto give a colorless suspension
  3. filtrationThe reaction mixture was filtered
  4. washthe solid support washed with DCM
  5. washThe combined filtrate was washed with saturated sodium thiosulfate (2×20 mL) and brine (1×20 mL)
  6. dry with materialThe organic phase was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resultant oil was purified via column chromatography with 100% DCM as mobile phase
  10. customto give 2.70 g (90%) of a colorless wax

Sources & evidence

ORD record
ord-e7a16d2f03174a678bab69dd6fd0fd67
Source dataset
uspto-grants-2015_04
Patent number
US09012225B2

Reaction notes

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